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1 Electronic Supplementary Material (ESI) for Soft Matter. This journal is The Royal Society of Chemistry 2017 Supporting Information Transition from nematic to gyroid-type cubic soft self-assembly by sidechain engineering of -conjugated sticky rods Marco Poppe, a Changlong Chen, b Helgard Ebert, a Silvio Poppe, a Marko Prehm, a Christoph Kerzig, a eng Liu b and Carsten Tschierske a a Institute of Chemistry, Martin-Luther University Halle-Wittenberg, Kurt-Mothes Str.2, D Halle/Saale, Germany. carsten.tschierske@chemie.uni-halle. b State Key Laboratory for Mechanical Behavior of Materials, Xi an Jiaotong University, Xi an , P. R. China. feng.liu@xjtu.edu.cn S1
2 1. Additional data 1.1 DSC traces a) b) H4 H6 c) d) H8 H12 e) H18 igure S1. DSC heating and cooling traces of compounds: a) H4, b) H6, c) H8, d) H12 and e) H18, recorded at 10 K min -1. S2
3 a) b) 6 10 c) d) e) f) igure S2. DSC heating and cooling traces of compounds: a) 6, b) 10, c) 12, d) 14, e) 16 and f) 18, recorded at 10 K min -1. S3
4 1.2 Additional textures a) b) Col hex c) Col hex d) Cub Cub Cr Cr e) N CybA f) Col hex 100 μm igure S3: Selected textures of compounds Hn as observed between crossed polarizers between non-treated microscopy slides: a) Iso-to-N CybA transition of H4 at 262 C, b-c) LC phases observed for H8 on rapid cooling; b) Col hex phase at T ~ 150 C; c) transition Col hex - Cub bi at T ~ 140 C and d) Cub bi phase with crystallization at T ~ 138 C, e) homeotropic N CybA phase of H6 at 200 C and f) Col hex phase of H12 at 170 C; arrows in e) indicate the orientation of polarizer and analyzer and the scale bar is given in f). S4
5 a) homeotropic N b) homeotropic SmA SmA N Cr d) c) Cub SmA Cub Colhex e) f) Cub 3D Colhex Colhex 200 μm igure S4: Selected textures of compounds n as observed between crossed polarizers between non-treated microscopy slides: a) texture at the NCybA-SmA transition of compound 8 at 181 C; b) SmA-phase of compound 8 at C; c) oily streaks texture of the SmA phase of 8 coexisting with the Cubbi/Ia3 d phase at 179 C; d) growth of the Cubbi/Ia3 d (black regions) and crystalline phase into the Colhex (green spherulitic region) of compound 16 at 149 C; e) Colhex phase of compound 18 at 140 C and f) development of the cubic phase (black areas) and, accompanied by a non-cubic birefringent 3D phase (uniformly colored mosaics) on cooling the Colhex phase of 18 at 124 C; the 3D phase occurs only at the Colhex-Cubbi phase transition and disappears on further cooling. S5
6 1.3 Additional XRD data Table S1: Experimental and calculated d-spacings, relative integrated intensities, and phases used in the reconstruction of electron densities for the Cub bi /Ia3 d phase for H10 at 160 ºC. All Intensities values are Lorentz and multiplicity corrected. (hkl) d obs. - spacings (nm) d cal. - spacings (nm) Intensity Phase (211) π (220) π (321) π (400) π (420) π (332) (422) (431) (521) (440) (532) 0.5 / (611) 1.0 / (541) / (631) / a cub = 9.17 nm Table S2: Experimental and calculated d-spacings, relative integrated intensities, and phases used in the reconstruction of electron densities for the Col hex /p6mm phase for H10 at 176 ºC. All intensities values are Lorentz and multiplicity corrected. (hk) d obs. - spacings (nm) d cal. - spacings (nm) Intensity Phase (10) (11) π (20) (21) π a hex = 4.31 nm S6
7 Table S3. Experimental and calculated d-spacings, relative integrated intensities, and phases used in the reconstruction of electron densities for the Cub bi /Ia3 d phase for 18 at 120 ºC. All Intensities values are Lorentz and multiplicity corrected. (hkl) d obs. - spacings (nm) d cal. - spacings (nm) Intensity Phase (211) π (220) π (321) π (420) π (332) (422) (521) (532) 0.2 / (611) 0.4 / (541) / (631) / (444) / (543) / (640) / (552) 0.7 / (633) / (721) 0.3 / (642) / a cub = 9.03 nm S7
8 Table S4. Experimental and calculated d-spacings, relative integrated intensities, and phases used in the reconstruction of electron densities for the Col hex /p6mm phase for 18 at 145 ºC. All intensities values are Lorentz and multiplicity corrected. (hk) d obs. - spacings (nm) d cal. - spacings (nm) Intensity Phase (10) (11) π (20) (21) π (30) a hex = 4.30 nm 200 I/a.u / igure S5: SAXS pattern of the N CybA phase of 8 at 186 o C. Table S5: Experimental and calculated d-spacings of the Cub bi /Ia3 d phases. a d Comp. T/ C 2 / / d obs /nm hkl d calc /nm obs - d calc /nm ,403 1,202 3, ,676 0,00 2,749 1,375 3, a cub /nm a 12 was reported in ref. [S1]; 16 could not be investigated due to rapid crystallization during exposure time; the /Ia3 d lattice was additionally supported by the absence of chiral domains S8
9 Table S6: Experimental and calculated d-spacings of the Col hex /p6mm phase of compounds H18 and 16. Comp. T/ C 2 / / d obs /nm hk d calc /nm d obs -d calc /nm a hex /nm (10) H (20) (20) (10) 3, (11) (20) a H12 was reported in ref. [S2]. a) 0.46 nm 600 b) 0.45 nm intensity/a.u intensity/a.u theta/ theta/ igure S6: WAXS pattern of compound H10 at a) 177 C (Col hex /p6mm) and b) 160 C (Cub/Ia3 d). S9
10 400 a) b) 0.44 nm 0.43 nm intensity/a.u nm intensity/a.u nm theta/ theta/ 300 c) 0.44 nm 400 d) 0.47 nm 200 intensity/a.u nm intensity/a.u nm theta/ theta/ igure S7: WAXS patterns of a) 8 at 185 C (nematic), b) 8 at 160 C (Cub/Ia3 d), c) 10 at 170 C (Cub/Ia3 d) and d) 16 at 160 C (Col hex /p6mm). Table S7: Structural data of the Col hex /p6mm LC-phases of compounds Hn and n a Comp a /nm V mol /nm³ V cell /nm³ n cell,cryst n cell,liq n cell,lc n Wall H H12 S H a V cell = volume of the unit cell defined by (3 ½ a hex 2 /2) x h with h = 0.46 nm corresponding to the maximum of the diffuse wide angle scattering; V mol = volume for a single molecule as calculated using the crystal volume increments; S3 n cell,cryst = V cell /V mol (average packing coefficient in the crystal is k = 0.7); S4 n cell, liq = number of molecules in the unit cell of an isotropic liquid with an average packing coefficient k = 0.55, calculated according to n cell, liq = 0.55/0.7 n cell, cryst ; n cell,lc = number of molecules in the unit cell in the LC phase estimated as the average of n cell,cryst and n cell,liq. n wall = number of molecules in the lateral cross section of the cylinder walls, calculated for the triangular honeycombs as n cell,lc /number of wall per unit cell = n cell,lc /3. n wall = means that on average molecules are laterally arranged in each hypothetical segment with h = 0.46 nm, i.e. there is a lateral staggering of the molecules in the cylinder walls or the packing of the aromatic cores is a bit closer than the assumed distance of 0.46 nm. S10
11 Table S8: Structural data of the cubic phases of compounds Hn and n. a Comp. H S a (nm) V cell (nm 3 ) V mol (nm 3 ) n cell,cryst = V cell / V mol n cell, liq n cell,lc Minimal Surface S (nm 2 ) n cell / S (molecules/nm -2 ) A mol (nm 2 ) d net (nm) a V cell = a cub 3 ; V mol = volume for a single molecule as calculated using the crystal volume increments; S3 for the calculations of n cell, cryst, n cell, liq and n cell,lc, see Table S7. S = area of the minimal surface in the unit cell of the Ia3 d phase S5 is S = a cub 2 ; S mol = molecular area on the minimal surface (S mol = S/n cell ). S6 d net = lateral distance between the two infinite networks of the cubic mesophase as determined by 3 ½ a cub /4. S5 2. Synthesis and analytical data General synthetic procedures P1: Cross-coupling reaction according to Sonogashira S7 : A mixture of 1,4-dialkoxy-2,5- diiodobenzene 4.n (1 equ.) and the appropriate acetylene (2.1 equ.) was dissolved in purified Et 3 N (50 ml/ 1 mmol). After degassing with argon for 30 min [Pd(PPh 3 ) 4 ] (3 mol%) and CuI (2 mol%) were added and the mixture was refluxed for 6 h. After removing the solvent the obtained residue was purified by column chromatography. In a similar way the syntheses of 2Si and 3Si were conducted by Sonogashira cross coupling of monovalent aryliodides using the molar ratios and catalyst given in the procedures in P2: Desilylation S2 : The appropriate silyl protected acetylene (1 equ.) and K 2 C 3 (5 equ) were dissolved in DCM/MeH (2:1; 15 ml/mmol) and stirred at 20 C. The progress of the reaction was recorded by TLC. The reaction was quenched with H 2 (50 ml) and the different phases were separated. The aqueous phase was extracted with DCM (3 x 50 ml). The combined organic phases were washed with water and brine. After drying over Na 2 S 4 S11
12 the solvent was removed under reduced pressure. The residue was purified by column chromatography. P3: Deprotection of the glycerol group with PPTS S8 : A mixture of the appropriate compound 5Hn or 5n (1 equ.) and PPTS (tip of a spatula) was dissolved in TH/MeH (1:1) and stirred at 50 C for 12 h. After finishing the reaction the solvent was removed and the residue was solved in DCM. The organic layer was washed with NaHC 3 solution (3 x 50 ml), water and brine. After drying over Na 2 S 4 the solvent was removed and the residue purified with column chromatography Synthesis of the 1,4-dialkoxy-2,5-diiodobenzenes I H H I + 2 C n H 2n+1 Br K 2 C 3 DM, 120 C 12-34% I C n H 2n+1 I 4.n C n H 2n+1 Scheme S1: Synthesis of the 1,4-dialkoxy-2,5-diiodobenzenes 4.n. 1,4-Dioctadecyloxy-2,5-diiodobenzene (4.18): A mixture of 1,4-dihydroxy-2,5- diiodobenzene (1.00 g, 2.8 mmol), n-bromooctadecane (2.30 g, 7.0 mmol), K 2 C 3 (1.90 g, 14.0 mmol) and Bu 4 NI (tip of a spatula) in anhydrous DM (50 ml) was stirred at 120 C for 12 h. After cooling to room temperature, the reaction was poured into water (50 ml) and the aqueous layer was extracted with Et 2 (3x50 ml). The combined organic layers were washed with saturated aqu. LiCl, water and brine. After drying over anhydrous Na 2 S 4, filtration and evaporation of the solvent, the crude product was purified by column chromatography (eluent: n-hexane). Colorless solid, C 42 H 76 I 2 2, M = g/mol, mp 82 C, yield: 0.76 g (32%), 1 H- NMR (400 MHz, CDCl 3 ) δ 7.17 (s, 2H, Ar H), 3.92 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 56H, CH 2 ), 0.87 (d, 3 J(H,H) = 7.0 Hz, 6H, CH 3 ) ppm Synthesis of 3-[4-(4-ethynylphenylethynyl)-2,3,5,6-tetrafluorophenyl]-1,2- isopropylidene-rac-glycerol (3) I H i 1 I H ii TMS TMS 2Si iii I TMS ii 2 H 3 H iii TMS 3Si Scheme S2: Synthesis of 3. Reagents and conditions: i) K 2 C 3, DM, 40 C, 3d, 59%, ii) NEt 3, [Pd(PPh 3 ) 4 ], CuI, 40 C, 12h, 94%, iii) K 2 C 3, DCM/MeH (2:1), 2h, 60-90%. S12
13 1,2-Isopropylidene-3-(2,3,5,6-tetrafluoro-4-iodophenyl)-rac-glycerol (1): According to the procedure described by Wen et al. S9 a mixture of pentafluoroiodobenzene (5.00 g, 17.0 mmol) and D,L-1,2-isopropylideneglycerole (2.91 g, 22.1 mmol) was solved in DM (50 ml) and stirred for 10 min at 20 C. After the stepwise addition of K 2 C 3 (3.04 g, 22.1 mmol) the reaction was stirred at 40 C for 48 h. The reaction was quenched with water und the phases were separated. The aqueous phase was extracted with Et 2 (3 x 50 ml). The combined organic phases were washed with water and brine. After drying over Na 2 S 4 the solvent was removed and the residue purified by column chromatography (eluent: CHCl 3 ). Colourless liquid; C 12 H 11 4 I 3 ; M = g/mol; yield: 4.86 g (70%). 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 1H, CH ), (m, 1H, CH 2 ), (m, 2H, CH 2 ), (m, 1H, CH 2 ), 1.42 (s, 3H, CH 3 ), 1.38 (s, 3H, CH 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (td, 3 J(,) = 10.2 Hz, 4 J(,) = 5.0 Hz, Ar ), (td, 3 J(,) = 10.1 Hz, 4 J(,) = 4.9 Hz, Ar ) ppm. 1,2-Isopropylidene-3-[2,3,5,6-tetrafluoro-4-(trimethylsilylethynyl)phenyl]-rac-glycerol (2Si): Synthesized according to P1 from 2 (4.86 g, 11.9 mmol), ethynyltrimethylsilane (1.50 g, 15.6 mmol), [Pd(PPh 3 ) 4 ] (0.42 g, 0.36 mmol) and CuI (0.05 g, 0.24 mmol). Purification by column chromatography (eluent: CHCl 3 /n-hexane = 1:1). Colourless liquid; C 17 H Si; M = g/mol; yield: 4.23 g (95%). 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 1H, CH ), (m, 1H, CH 2 ), (m, 2H, CH 2 ), (m, 1H, CH 2 ), 1.42 (s, 3H, CH 3 ), 1.38 (s, 3H, CH 3 ), 0.32 (s, 9H, Si (CH 3 ) 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (td, 3 J(,) = 10.7 Hz, 4 J(,) = 4.0 Hz, Ar ), (td, 3 J(,) = 10.6 Hz, 4 J(,) = 3.9 Hz, Ar ) ppm. 3-(4-Ethynyl-2,3,5,6-tetrafluorophenyl)-1,2-isopropylidene-rac-glycerol (2): Synthesized according to P2 from 3 (4.23 g, 11.3 mmol) and K 2 C 3 (7.76 g, 56.3 mmol). Purification by column chromatography (eluent: CHCl 3 /n-hexane = 1:1). Colourless liquid; C 14 H ; M = g/mol; yield: 3.36 g (98%). 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 1H, CH ), (m, 1H, CH 2 ), (m, 2H, CH 2 ), (m, 1H, CH 2 ), 3.55 (s, 1H, CH), 1.42 (s, 3H, CH 3 ), 1.38 (s, 3H, CH 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (td, 3 J(,) = 10.7 Hz, 4 J(,) = 4.0 Hz, Ar ), (td, (,) = 10.6 Hz, 4 J(,) = 3.9 Hz, Ar ) ppm. 3-{4-[4-(Trimethylsilylethynyl)phenylethynyl]-2,3,5,6-tetrafluorophenyl}-1,2-isopropylidene-rac-glycerol (3Si): Synthesized according to P1 from 4 (3.37 g, 11.1 mmol), (4- iodophenylethynyl)trimethylsilane (3.66 g, 12.2 mmol), [Pd(PPh 3 ) 2 Cl 2 ] (0.24 g, 0.3 mmol) and CuI (0.06 g, 0.31 mmol). Purification by column chromatography (eluent: CHCl 2 /nhexane = 4:1). Colorless solid; C 25 H Si; M = g/mol; yield: 3.23 g (61%); mp = 95 C. 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 4H, Ar H), (m, 1H, CH ), 4.33 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.1 Hz, 1H, CH 2 ), 4.23 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.6 Hz, 1H, CH 2 ), (m, 1H, CH 2 ), (m, 1H, CH 2 ), 1.43 (s, 3H, CH 3 ), 1.38 (s, 3H, CH 3 ), 0.26 (s, 9H, Si (CH 3 ) 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (td, 3 J(,) = 10.2 Hz, 4 J(,) = 3.4 Hz, Ar ), (td, 3 J(,) = 9.8 Hz, 4 J(,) = 2.9 Hz, Ar ) ppm. 3-[4-(4-Ethynylphenylethynyl)-2,3,5,6-tetrafluorophenyl]-1,2-isopropylidene-racglycerol (3): Synthesized according to P2 from 5 (3.23 g, 6.8 mmol) and K 2 C 3 (4.70 g, 33.9 mmol). Purification by column chromatography (eluent: CHCl 2 /n-hexane = 4:1). Yellow solid; C 22 H ; M = g/mol; yield: 1.22 g (44%); mp = 42 C. 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 4H, Ar H), (m, 1H, CH ), 4.33 (dd, 2 J(H,H) = 10.1 S13
14 Hz, 3 J(H,H) = 5.1 Hz, 1H, CH 2 ), 4.24 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.6 Hz, 1H, CH 2 ), 4.16 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 6.5 Hz, 1H, CH 2 ), 3.96 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 1H, CH 2 ), 3.20 (s, 1H, CH), 1.43 (s, 3H, CH 3 ), 1.38 (s, 3H, CH 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (td, 3 J(,) = 10.2 Hz, 4 J(,) = 3.4 Hz, Ar ), (td, (,) = 9.8 Hz, 4 J(,) = 2.8 Hz, Ar ) ppm Synthesis of the fluorinated and non fluorinated acetonides Scheme S3: Synthesis of the fluorinated and non fluorinated acentonides 5Hn and 5n. 1,4-Dibutyloxy-2,5-bis{4-[4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (5H4): Synthesized according to P1 from 4.4 (133 mg, 0.28 mmol), 3H (195 mg, 0.59 mmol), [Pd(PPh 3 ) 4 ] (9.7 mg, mmol), CuI (1.1 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 58 H 58 8, M = g/mol, mp 210 C, yield: 250 mg (95%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 12H, Ar H), 7.01 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H, CH ), 4.18 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), 3.97 (dd, 2 J(H,H) = 9.5 Hz, 3 J(H,H) = 5.8 Hz, 2H, CH 2 ), 3.91 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 5.8 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), 1.47 (s, 3H, CH 3 ), 1.41 (s, 3H, CH 3 ), 1.01 (t, 3 J(H,H) = 7.4 Hz, 3H, CH 3 ) ppm. 1,4-Dihexyloxy-2,5-bis{4-[4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (5H6): Synthesized according to P1 from 4.6 (328 mg, 0.75 mmol), 3H (600 mg, 1.81 mmol), [Pd(PPh 3 ) 4 ] (26.2 mg, mmol), CuI (2.9 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 62 H 66 8, M = g/mol, yield: 371 mg (53%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 12H, Ar H), 6.99 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H, CH ), 4.16 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) 6.4 Hz, 2H, CH 2 ), (m, 6H, CH 2 ), 3.95 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 5.9 Hz, 2H, CH 2 ), 3.89 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 5.8 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), 1.45 (s, 6H, CH 3 ), 1.39 (s, 6H, CH 3 ), (m, 8H, CH 2 ), 0.89 (t, 3 J(H,H) = 7.1 Hz, 6H, CH 3 ) ppm. S14
15 1,4-Dioctyloxy-2,5-bis{4-[4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (5H8): Synthesized according to P1 from 4.8 (147 mg, 0.25 mmol), 3H (175 mg, 0.52 mmol), [Pd(PPh 3 ) 4 ] (8.7 mg, mmol), CuI (1.0 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 66 H 74 8, M = g/mol, mp, 157 C, yield: 250 mg (95%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 12H, Ar H), 7.01 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H), 4.18 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH ), (m, 4H, CH 2 ), 3.97 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 5.9 Hz, 2H, CH 2 ), 3.91 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 5.8 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 34H, CH 2, CH 3 ), 0.88 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 1,4-Didecyloxy-2,5-bis{4-[4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (5H10): Synthesized according to P1 from 4.10 (122 mg, 0.20 mmol), 3H (139 mg, 0.42 mmol), [Pd(PPh 3 ) 4 ] (6.9 mg, mmol), CuI (0.7 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ).Yellow solid, C 70 H 82 8, M = g/mol, mp 142 C, yield: 200 mg (95%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 12H, Ar H), 7.01 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H, CH ), 4.18 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), 4.08 (dd, 2 J(H,H) = 9.5 Hz, 3 J(H,H) = 5.4 Hz, 2H, CH 2 ), 4.04 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 CH 2 ), 3.97 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 5.9 Hz, 2H, CH 2 ), 3.91 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 5.8 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 40H, CH 2, CH 3 ), 0.88 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 1,4-Dioctadecyloxy-2,5-bis{4-[4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (5H18): Synthesized according to P1 from 4.18 (310 mg, 0.40 mmol), 3H (315 mg, 0.95 mmol), [Pd(PPh 3 ) 4 ] (14.0 mg, mmol), CuI (2.0 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 86 H 114 8, M = g/mol, yield: 93 mg (18%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 12H, Ar H), 6.99 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H, CH ), 4.16 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 6.5 Hz, 2H, CH 2 ), 4.06 (dd, 2 J(H,H) = 9.5 Hz, 3 J(H,H) = 5.4 Hz, 2H, CH 2 ), 4.02 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), 3.95 (dd, 2 J(H,H) = 9.5 Hz, 3 J(H,H) = 5.9 Hz, 2H, CH 2 ), 3.89 (dd, 2 J(H,H) = 8.5 Hz, 3 J(H,H) = 5.8 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), 1.45 (s, 6H, CH 3 ), (m, 62H, CH 2 ), 0.85 (t, 3 J(H,H) = 6.8 Hz, 6H, CH 3 ) ppm. 1,4-Dihexyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (56): Synthesized according to P1 from 4.6 (122 mg, 0.23 mmol), 3 (196 mg, 0.48 mmol), [Pd(PPh 3 ) 4 ] (7.9 mg, mmol), CuI (0.9 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 62 H , M = g/mol, mp 146 C, yield: 240 mg (96%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 8H, Ar H), 7.02 (s, 2H, Ar H), (m, 2H, CH ), 4.34 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.1 Hz, 2H, CH 2 ), 4.24 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), 4.16 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), 4.04 (t, 3 J(H,H) = 6.5 Hz, 4H, CH 2 ), 3.96 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 24H, CH 2, CH 3 ), 0.91 (t, 3 J(H,H) = S15
16 7.1 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (m, Ar ), (m, Ar ) ppm. 1,4-Dioctyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (58): Synthesized according to P1 from 4.8 (129 mg, 0.22 mmol), 3 (185 mg, 0.46 mmol), [Pd(PPh 3 ) 4 ] (5.2 mg, mmol), CuI (0.8 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 66 H , M = g/mol, mp 135 C, yield: 240 mg (95%), 1 H-NMR (500 MHz, CDCl 3 ) δ (m, 8H, Ar H), 7.03 (s, 2H, Ar H), (m, 2H, CH ), 4.35 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.2 Hz, 2H, CH 2 ), 4.25 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), 4.18 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), 4.05 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), 3.98 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 32H, CH 2, CH 3 ), 0.89 (t, 3 J(H,H) = 6.8 Hz, 6H, CH 3 ) ppm. 19 -NMR (470 MHz, CDCl 3 ) δ (td, 3 J(,) = 9.9 Hz, 4 J(,) = 3.0 Hz, Ar ), (td, 3 J(,) = 9.7 Hz, 4 J(,) = 2.6 Hz, Ar ) ppm. 1,4-Didecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(1,2-isopropylidene-rac-glycero-3)phenylethynyl]phenylethynyl}benzene (510): Synthesized according to P1 from 4.10 (135 mg, 0.21 mmol), 3 (178 mg, 0.44 mmol), [Pd(PPh 3 ) 4 ] (7.3 mg, mmol), CuI (0.8 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 70 H , M = g/mol, mp 141 C, yield: 230 mg (92%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 8H, Ar H), 7.02 (s, 2H, Ar H), (m, 2H, CH ), 4.34 (dd, 2 J(H,H) = 10.2 Hz, 3 J(H,H) = 5.1 Hz, 2H, CH 2 ), 4.24 (dd, 2 J(H,H) = 10.2 Hz, 3 J(H,H) = 5.5 Hz, 2H, CH 2 ), 4.16 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), 4.04 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), 3.96 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 40H, CH 2, CH 3 ), 0.87 (t, 3 J(H,H) = 7.0 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (m, Ar ), (m, Ar ) ppm. 1,4-Didodecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(1,2-isopropylidene-rac-glycero- 3)phenylethynyl]phenylethynyl}benzene (512): Synthesized according to P1 from 4.12 (119 mg, 0.17 mmol), 3 (144 mg, 0.36 mmol), [Pd(PPh 3 ) 4 ] (3.6 mg, mmol), CuI (0.6 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 74 H , M = g/mol, mp 126 C, yield: 210 mg (95%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 8H, Ar H), 7.02 (s, 2H, Ar H), (m, 2H, CH), 4.33 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.1 Hz, 2H, CH 2 ), 4.24 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), 4.16 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 6.5 Hz, 2H, CH 2 ), 4.04 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), 3.96 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 8H, CH 2 ), (m, 48H, CH 2, CH 3 ), 0.86 (t, 3 J(H,H) = 6.7 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (m, Ar ), (m, Ar ) ppm. 1,4-Ditetradecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(1,2-isopropylidene-rac-glycero- 3)phenylethynyl]phenylethynyl}benzene (514): Synthesized according to P1 from 4.14 S16
17 (144 mg, 0.19 mmol), 3 (161 mg, 0.40 mmol), [Pd(PPh 3 ) 4 ] (6.6 mg, mmol), CuI (0.7 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 78 H , M = g/mol, mp 135 C, yield: 220 mg (88%), 1 H-NMR (400 MHz, CDCl 3 ) δ (m, 8H, Ar H), 7.02 (s, 2H, Ar H), (m, 2H, CH ), 4.34 (dd, 2 J(H,H) = 10.0 Hz, 3 J(H,H) = 5.1 Hz, 2H, CH 2 ), 4.24 (dd, 2 J(H,H) = 10.0 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), 4.16 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), 4.04 (t, 3 J(H,H) = 6.5 Hz, 4H, CH 2 ), 3.96 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 56H, CH 2, CH 3 ), 0.86 (t, 3 J(H,H) = 6.8 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, CDCl 3 ) δ (td, 3 J(,) = 10.2 Hz, 4 J(,) = 3.3 Hz, Ar ), (td, 3 J(,) = 9.8 Hz, 4 J(,) = 2.8 Hz, Ar ) ppm. 1,4-Dihexadecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(1,2-isopropylidene-rac-glycero- 3)phenylethynyl]phenylethynyl}benzene (516): Synthesized according to P1 from 4.16 (148 mg, 0.18 mmol), 3 (155 mg, 0.38 mmol), [Pd(PPh 3 ) 4 ] (6.2 mg, mmol), CuI (0.7 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 82 H , M = g/mol, mp 89 C, yield: 240 mg (95%), 1 H-NMR (500 MHz, CDCl 3 ) δ (m, 8H, Ar H), 7.03 (s, 2H, Ar H), (m, 2H, CH ), 4.35 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.0 Hz, 2H, CH 2 ), 4.25 (dd, 2 J(H,H) = 10.2 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), 4.18 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), 4.05 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), 3.98 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 64H, CH 2, CH 3 ), 0.88 (t, 3 J(H,H) = 7.1 Hz, 6H, CH 3 ) ppm. 19 -NMR (470 MHz, CDCl 3 ) δ (m, Ar ), (m, Ar ) ppm. 1,4-Dioctadecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(1,2-isopropylidene-rac-glycero- 3)phenylethynyl]phenylethynyl}benzene (518): Synthesized according to P1 from 4.18 (152 mg, 0.17 mmol), 3 (144 mg, 0.36 mmol), [Pd(PPh 3 ) 4 ] (3.5 mg, mmol), CuI (0.6 mg, mmol) in NEt 3 (50 ml). Purification by column chromatography (eluent: CHCl 3 ). Yellow solid, C 86 H , M = g/mol, mp 128 C, yield: 240 mg (95%), 1 H-NMR (500 MHz, CDCl 3 ) δ (m, 8H, Ar H), 7.03 (s, 2H, Ar H), (m, 2H, CH ), 4.35 (dd, 2 J(H,H) = 10.2 Hz, 3 J(H,H) = 5.0 Hz, 2H, CH 2 ), 4.25 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), 4.18 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 6.4 Hz, 2H, CH 2 ), 4.05 (t, 3 J(H,H) = 6.5 Hz, 4H, CH 2 ), 3.98 (dd, 2 J(H,H) = 8.6 Hz, 3 J(H,H) = 5.6 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), (m, 72H, CH 2, CH 3 ), 0.89 (t, 3 J(H,H) = 7.0 Hz, 6H, CH 3 ) ppm. 19 -NMR (470 MHz, CDCl 3 ) δ (td, 3 J(,) = 9.9 Hz, 4 J(,) = 3.0 Hz, Ar ), (td, 3 J(,) = 9.6 Hz, 4 J(,) = 2.5 Hz, Ar ) ppm. S17
18 2.2.5 Synthesis of compounds Hn and n X X C n H 2n+1 X X X X H X X 2n+1 C n 5Hn (X= H) 5n (X= ) PPTS 40 C, 55-70% TH/MeH X X C n H 2n+1 X X H H H X X H 2n+1 C n X X H Hn (X=H) n (X=) Scheme S4: Synthesis of compounds Hn and n. 1,4-Dibutyloxy-2,5-bis{4-[4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (H4): Synthesized according to P3 from 5H4 (250 mg, 0.28 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 52 H 50 8, M = g/mol, yield: 183 mg (81%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), (m, 4H, Ar H), 7.45 (s, 2H, Ar H), (m, 4H, Ar H), 6.94 (br, 2H, H), 6.54 (br, 2H, H), (m, 2H, CH ), 4.52 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 4.3 Hz, 2H, CH 2 ), 4.43 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H)= 6.3 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), 4.09 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), 0.95 (t, 3 J(H,H) = 7.4 Hz, 6H, CH 3 ) ppm. 13 C-NMR (126 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar H), (C Ar H), , , , , , , ( C C ), ( C C ), ( C C ), ( C C ), (HCH 2 ), 70.86, 69.21, 64.04, ( CH 2 ), 19.34, ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 52 H 50 8 Li, ; found Anal. Calcd. for C 52 H 50 8 H 2 : C, 76.08; H, ound: C, 76.21; H, ,4-Dihexyloxy-2,5-bis{4-[4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (H6): Synthesized according to P3 from 5H6 (371 mg, 0.40 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 56 H 58 8, M = g/mol, yield: 100 mg (29%), 1 H-NMR (500 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), (m, 4H, Ar H), 7.41 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H, CH ), 4.45 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 4.3 Hz, 2H, CH 2 ), 4.37 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 6.3 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), 4.04 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 8H, CH 2 ), 0.81 (t, 3 J(H,H) = 7.0 Hz, 6H, CH 3 ) ppm. 13 C-NMR (126 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar H), (C Ar H), , , , , , ( C C ), ( C C ), ( C C ), S18
19 ( C C ), (HCH 2 ), 70.82, 69.48, 63.99, ( CH 2 ), 29.31, 25.77, 22.62, ( CH 3 ) ppm. HRMS (m/z): [M]+Cl-calcd. for C 56 H 58 8 Cl, ; found ,4-Dioctyloxy-2,5-bis{4-[4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (H8): Synthesized according to P3 from 5H8 (250 mg, 0.25 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 60 H 66 8 ; M = g/mol, yield: 208 mg (90%), 1 H-NMR (500 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), (m, 4H, Ar H), 7.49 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H, CH ), 4.51 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 4.3 Hz, 2H, CH 2 ), 4.43 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 6.3 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), 4.13 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 16H, CH 2 ), 0.87 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 13 C-NMR (126 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar H), (C Ar H), , , , , , ( C C ), ( C C ), ( C C ), ( C C ), (HCH 2 ), 70.86, 69.55, 64.03, ( CH 2 ), 29.42, 29.38, 29.35, 26.19, 22.69, ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 60 H 66 8, ; found Anal. Calcd. for C 60 H 66 8 H 2 : C, 77.22; H, ound: C, 77.68; H, ,4-Didecyloxy-2,5-bis{4-[4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (H10): Synthesized according to P3 from 5H10 (200 mg, 0.20 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 64 H 74 8, M = g/mol, yield: 153 mg (81%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), (m, 4H, Ar H), 7.49 (s, 2H, Ar H), (m, 4H, Ar H), 6.94 (br, 2H, H), 6.56 (br, 2H, H), (m, 2H, CH ), 4.52 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 4.3 Hz, 2H, CH 2 ), 4.43 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 6.3 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), 4.14 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 24H, CH 2 ), 0.89 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 13 C-NMR (101 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar H), (C Ar H), , , , , , ( C C ), ( C C ), ( C C ), ( C C ), (HCH 2 ), 72.36, 71.06, 69.11, 65.53, ( CH 2 ), 31.25, 31.11, 30.97, 30.90, 27.73, 27.09, 24.23, ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 64 H 74 8 Li, , found Anal. Calcd. for C 64 H 74 8 H 2 : C, 77.70; H, ound: C, 77.65; H, ,4-Dioctadecyloxy-2,5-bis{4-[4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (H18): Synthesized according to P3 from 5H18 (93 mg, 0.07 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 80 H 106 8, M = g/mol, yield: 20 mg (23%), 1 H-NMR (500 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), (m, 4H, Ar H), 7.43 (s, 2H, Ar H), (m, 4H, Ar H), (m, 2H, CH ), 4.46 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 4.4 Hz, 2H, CH 2 ), 4.37 (dd, 2 J(H,H) = 9.6 Hz, 3 J(H,H) = 6.3 Hz, 2H, CH 2 ), (m, 4H, CH 2 ), 4.09 (t, 3 J(H,H) = 6.3 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 56H, CH 2 ), 0.82 (t, 3 J(H,H) = 7.0 Hz, 6H, CH 3 ) ppm. 13 C-NMR (126 S19
20 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar H), (C Ar H), , , , , , , , , , , , , , , , , , , , ( C C ), ( C C ), ( C C ), ( C C ), (HCH 2 ), 71.08, 70.83, 64.00, ( CH 2 ), 29.75, 29.72, 29.66, 29.35, 26.19, 22.67, ( CH 3 ) ppm. HRMS (m/z): [M]+Clcalcd. for C 80 H Cl, ; found ,4-Dihexyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (6): Synthesized according to P3 from 56 (93 mg, 0.07 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 56 H , M = g/mol, yield: 175 mg (79%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), 7.50 (s, 2H, Ar H), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 2H, CH ), (m, 4H, CH 2 ), 4.12 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 8H, CH 2 ), 0.88 (t, 3 J(H,H) = 7.0 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, pyridine-d 5 ) δ (m, Ar ), (m, Ar ) ppm. 13 C-NMR (101 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar ), (C Ar ), (C Ar H), , , , , , ( C C ), ( C C ), ( C C ), (HCH 2 ), 72.05, 69.83, 63.84, ( CH 2 ), 29.64, 26.12, 22.97, ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 56 H Li, , found Anal. Calcd. for C 56 H H 2 : C, 65.83; H, ound: C, 65.91; H, ,4-Dioctyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (8): Synthesized according to P3 from 58 (240 mg, 0.21 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 60 H , M = g/mol, yield: 160 mg (72%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), 7.54 (s, 2H, Ar H), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 2H, CH ), (m, 4H, CH 2 ), 4.18 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 16H, CH 2 ), 0.91 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, pyridine-d 5 ) δ (m, Ar ), (m, Ar ) ppm. 13 C- NMR (126 MHz, pyridine-d 5 ) δ ( CH 2 ), (C Ar ), (C Ar H), , , , , ( C C ), ( C C ), ( HCH 2 ), 77.57, 71.74, 69.56, 63.53, ( CH 2 ), 29.41, 29.39, 29.36, 26.20, 22.70, ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 60 H Li, ; found analysis (calcd. for C 60 H H 2 ): C (66.91, 66.83), H (5.61, 5.50). Anal. Calcd. for C 60 H H 2 : C, 66.91; H, ound: C, 66.83; H, ,4-Didecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (10): Synthesized according to P3 from 510 (230 mg, 0.21 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 64 H , M = g/mol, yield: 181 mg (77%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, S20
21 Ar H), (m, 4H, Ar H), 7.51 (s, 2H, Ar H), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 2H, CH ), (m, 4H, CH 2 ), 4.15 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 20H, CH 2 ), 0.89 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, pyridine-d 5 ) δ (m, Ar ), (m, Ar ) ppm. 13 C- NMR (126 MHz, pyridine-d 5 ) δ ( CH 2 ), (C Ar ), (C Ar H), , , , , ( C C ), ( C C ), ( C C ), (HCH 2 ), 77.57, 77.55, 76.40, 71.74, 69.56, 63.53, ( CH 2 ), 29.76, 29.62, 29.47, 29.43, 29.40, 26.24, 22.73, ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 64 H Li, , found Anal. Calcd. for C 64 H H 2 : C, 67.83; H, ound: C, 67.54; H, ,4-Didodecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (12): Synthesized according to P3 from 512 (210 mg, 0.18 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 68 H , M = g/mol, yield: 143 mg (72%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), 7.51 (s, 2H, Ar H), 7.13 (d, 3 J(H,H) = 5.1 Hz, 2H, H), 6.65 (t, 3 J(H,H) = 5.4 Hz, 2H, H), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 2H, CH ), 4.23 (t, 3 J(H,H) = 5.2 Hz, 4H, CH 2 ), 4.16 (pt, 3 J(H,H) = 6.1 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 32H, CH 2 ), 0.89 (t, 3 J(H,H) = 6.3 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, pyridine-d 5 ) δ (m, Ar ), (m, Ar ) ppm. 13 C- NMR (126 MHz, pyridine-d 5 ) δ ( CH 2 ), (C Ar ), , , (C Ar H), ( C C ), ( C C ), ( C C ), (HCH 2 ), 77.09, 72.44, 70.26, 64.23, ( CH 2 ), 30.47, 30.40, 30.38, 30.17, 30.13, 30.11, 26.94, ( CH 2 ), ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 68 H Li, ; found Anal. Calcd. for C 68 H H 2 : C, 67.65; H, ound: C, 67.65; H, ,4-Ditetradecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(rac-glycero-1)phenylethynyl]- phenylethynyl}benzene (14): Synthesized according to P3 from 514 (220 mg, 0.17 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 72 H , M = g/mol, yield: 154 mg (74%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), 7.51 (s, 2H, Ar H), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 2H, CH ), (m, 4H, CH 2 ), 4.16 (t, 3 J(H,H) = 6.3 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 40H, CH 2 ), 0.88 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, pyridine-d 5 ) δ (m, Ar ), (m, Ar ) ppm. 13 C- NMR (101 MHz, pyridine-d 5 ) δ ( CH 2 ), (C Ar ), (C Ar H), , , , , , ( C C ), ( C C ), ( C C ), (HCH 2 ), 76.38, 75.20, 70.54, 68.36, 62.33, ( CH 2 ), 28.60, 28.58, 28.52, 28.50, 28.28, 28.23, 28.21, 25.04, 21.52, ( CH 3 ). HRMS (m/z): [M]+Li + -calcd. for C 72 H Li, , found Anal. Calcd. for C 72 H H 2 : C, 68.45; H, ound: C, 68.65; H, S21
22 1,4-Dihexadecylloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(rac-glycero-1)phenylethynyl]- phenylethynyl}benzene (16): Synthesized according to P3 from 516 (240 mg, 0.17 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 76 H , M = g/mol, yield: 181 mg (83%), 1 H-NMR (500 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), 7.51 (s, 2H, Ar H), 4.90 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 4.0 Hz, 2H, CH 2 ), 4.80 (dd, 2 J(H,H) = 10.1 Hz, 3 J(H,H) = 6.3 Hz, 2H, CH 2 ), (m, 2H, CH ), (m, 4H), 4.16 (t, 3 J(H,H) = 6.4 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 48H, CH 2 ), 0.88 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 19 -NMR (470 MHz, pyridine-d 5 ) δ (m, Ar ), (m, Ar ) ppm. 13 C-NMR (101 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar ), (C Ar H), , , , , ( C C ), ( C C ), ( C C ), ( C C ), (HCH 2 ), 76.35, 75.20, 70.53, 68.36, 62.33, ( CH 2 ), 28.61, 28.59, 28.58, 28.51, 28.28, 28.23, 28.20, 25.04, 21.51, ( CH 2 ). HRMS (m/z): [M]+Li + -calcd. for C 76 H Li, , found Anal. Calcd. for C 76 H H 2 : C, 70.13; H, ound: C, 70.24; H, ,4-Dioctadecyloxy-2,5-bis{4-[2,3,5,6-tetrafluoro-4-(rac-glycero-1)phenylethynyl]phenylethynyl}benzene (18): Synthesized according to P3 from 518 (240 mg, 0.17 mmol) and PPTS (tip of a spatula) in MeH/TH (1:1, 30 ml:30 ml). Purification by column chromatography (eluent: CHCl 3 :MeH = 9:1). Yellow-greenish solid, C 80 H , M = g/mol, yield: 201 mg (88%), 1 H-NMR (400 MHz, pyridine-d 5 ) δ (m, 4H, Ar H), (m, 4H, Ar H), 7.51 (s, 2H, Ar H), (m, 2H, CH 2 ), (m, 2H, CH 2 ), (m, 2H, CH ), (m, 4H, CH 2 ), 4.16 (t, 3 J(H,H) = 6.3 Hz, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 4H, CH 2 ), (m, 56H, CH 2 ), 0.88 (t, 3 J(H,H) = 6.9 Hz, 6H, CH 3 ) ppm. 19 -NMR (376 MHz, pyridine-d 5 ) δ (m, Ar ), (m, Ar ) ppm. 13 C- NMR (101 MHz, pyridine-d 5 ) δ ( CH 2 ), ( CH 2 ), (C Ar ), (C Ar H), , , , , ( C C ), ( C C ), (HCH 2 ), 70.53, 68.36, 62.33, ( CH 2 ), 28.60, 28.58, 28.50, 28.27, 28.23, 28.19, 25.04, 21.51, ( CH 3 ) ppm. HRMS (m/z): [M]+Li + -calcd. for C 80 H Li, ; found Anal. Calcd. for C 80 H H 2 : C, 70.77; H, ound: C, 70.55; H, S22
23 3. Representative NMR spectra 3.1 NMR spectra of H10 CH 2 igure S8: 1 H-NMR spectra of H10 (400 MHz, pyridine-d 5 ). S23
24 MPoppe_2496_APT_08Sep2016_ MPoppe_2496 MPP f1 (ppm) igure S9: 13 C-NMR (APT) spectra of H10 (101 MHz, pyridine-d 5 ). S24
25 3.2 NMR spectra of 10 igure S10: 1 H-NMR spectra of 10 (400 MHz, pyridine-d 5 ). S25
26 igure S11: 19 -NMR spectra of 10 (176 MHz, pyridine-d 5 ). S26
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